DE3546123A1 - Verfahren zur herstellung von aldehyden - Google Patents
Verfahren zur herstellung von aldehydenInfo
- Publication number
- DE3546123A1 DE3546123A1 DE19853546123 DE3546123A DE3546123A1 DE 3546123 A1 DE3546123 A1 DE 3546123A1 DE 19853546123 DE19853546123 DE 19853546123 DE 3546123 A DE3546123 A DE 3546123A DE 3546123 A1 DE3546123 A1 DE 3546123A1
- Authority
- DE
- Germany
- Prior art keywords
- rhodium
- concentration
- catalyst
- aqueous solution
- sulfonated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 41
- 239000010948 rhodium Substances 0.000 claims abstract description 40
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
- -1 aliphatic olefins Chemical class 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 40
- 150000001336 alkenes Chemical class 0.000 abstract description 11
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 6
- 239000003446 ligand Substances 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
- 150000003003 phosphines Chemical class 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical class [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 2
- 229910003450 rhodium oxide Inorganic materials 0.000 description 2
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- MNEMJPSCBXIKTP-UHFFFAOYSA-N 4,4-dimethylnon-1-ene Chemical compound CCCCCC(C)(C)CC=C MNEMJPSCBXIKTP-UHFFFAOYSA-N 0.000 description 1
- PHLSZZJPMMNIKI-UHFFFAOYSA-L Cl[Rh](Cl)C1=CC=CCCCC1 Chemical compound Cl[Rh](Cl)C1=CC=CCCCC1 PHLSZZJPMMNIKI-UHFFFAOYSA-L 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- WVIVIPPDKDWCKI-UHFFFAOYSA-H [Rh+3].[Rh+3].[O-]C(=O)CC([O-])=O.[O-]C(=O)CC([O-])=O.[O-]C(=O)CC([O-])=O Chemical compound [Rh+3].[Rh+3].[O-]C(=O)CC([O-])=O.[O-]C(=O)CC([O-])=O.[O-]C(=O)CC([O-])=O WVIVIPPDKDWCKI-UHFFFAOYSA-H 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000005228 aryl sulfonate group Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853546123 DE3546123A1 (de) | 1985-12-24 | 1985-12-24 | Verfahren zur herstellung von aldehyden |
| YU1967/86A YU45381B (en) | 1985-12-24 | 1986-11-18 | Process for making aldehide |
| KR1019860010601A KR890003750B1 (ko) | 1985-12-24 | 1986-12-11 | 알데히드의 제조방법 |
| RO125839A RO95854B (ro) | 1985-12-24 | 1986-12-12 | Procedeu pentru obtinerea aldehidelor |
| AT86117394T ATE73122T1 (de) | 1985-12-24 | 1986-12-13 | Verfahren zur herstellung von aldehyden. |
| ES198686117394T ES2037006T3 (es) | 1985-12-24 | 1986-12-13 | Procedimiento para la fabricacion de aldehidos. |
| EP86117394A EP0226988B1 (de) | 1985-12-24 | 1986-12-13 | Verfahren zur Herstellung von Aldehyden |
| DE8686117394T DE3684113D1 (de) | 1985-12-24 | 1986-12-13 | Verfahren zur herstellung von aldehyden. |
| JP61299065A JPS62153238A (ja) | 1985-12-24 | 1986-12-17 | アルデヒドの製造法 |
| HU865260A HUT42047A (en) | 1985-12-24 | 1986-12-17 | Process for preparing aldehydes |
| CS869413A CS264286B2 (en) | 1985-12-24 | 1986-12-17 | Process for preparing aldehydes |
| IE328886A IE59957B1 (en) | 1985-12-24 | 1986-12-17 | Process for the preparation of aldehydes |
| ZA869473A ZA869473B (en) | 1985-12-24 | 1986-12-17 | Process for the preparation of aldehydes |
| BR8606417A BR8606417A (pt) | 1985-12-24 | 1986-12-23 | Processo para a preparacao de aldeidos |
| AU66896/86A AU598502B2 (en) | 1985-12-24 | 1986-12-23 | Process for the preparation of aldehydes |
| CA000526281A CA1263407A (en) | 1985-12-24 | 1986-12-24 | Process for the preparation of aldehydes |
| US07/193,956 US4808757A (en) | 1985-12-24 | 1988-05-13 | Process for the preparation of aldehydes |
| HRP-1967/86A HRP940741A2 (en) | 1985-12-24 | 1994-10-24 | Process for the preparation of aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853546123 DE3546123A1 (de) | 1985-12-24 | 1985-12-24 | Verfahren zur herstellung von aldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3546123A1 true DE3546123A1 (de) | 1987-06-25 |
Family
ID=6289576
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853546123 Withdrawn DE3546123A1 (de) | 1985-12-24 | 1985-12-24 | Verfahren zur herstellung von aldehyden |
| DE8686117394T Expired - Fee Related DE3684113D1 (de) | 1985-12-24 | 1986-12-13 | Verfahren zur herstellung von aldehyden. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686117394T Expired - Fee Related DE3684113D1 (de) | 1985-12-24 | 1986-12-13 | Verfahren zur herstellung von aldehyden. |
Country Status (17)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| DE4207922A1 (de) * | 1992-03-13 | 1993-09-23 | Pharmatech Gmbh | Wasserloesliche einschlussverbindungen und verfahren zu deren herstellung |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3640614A1 (de) * | 1986-11-27 | 1988-06-09 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| PT91161A (pt) * | 1988-07-14 | 1990-02-08 | Union Carbide Chem Plastic | Processo aperfeicoado para a producao de alcoois e aldeidos |
| US5223648A (en) * | 1990-12-17 | 1993-06-29 | Hoechst Aktiengesellschaft | Process for producing aldehydes |
| US5261889A (en) * | 1992-11-24 | 1993-11-16 | Boston Scientific Corporation | Injection therapy catheter |
| DE4242725A1 (de) * | 1992-12-17 | 1994-06-23 | Hoechst Ag | Verfahren zur Herstellung von höheren, vorwiegend unverzweigten, primären Alkoholen |
| US5300617A (en) * | 1993-01-21 | 1994-04-05 | Exxon Chemical Patents Inc. | Potassium para-diphenyl phosphino benzene sulfonate ligand |
| DE4427428A1 (de) | 1994-08-03 | 1996-02-29 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE102008044783B4 (de) * | 2008-08-28 | 2012-05-16 | Oxea Gmbh | Verfahren zur Gewinnung von aliphatischen C3- bis C10- Aldehyden aus Hochsiedern durch thermische Behandlung |
| CN104045532B (zh) * | 2013-03-15 | 2018-05-25 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4248802A (en) * | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| FR2314910A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede d'hydroformylation des olefines |
| GB2086906B (en) * | 1979-02-12 | 1983-08-17 | Exxon Research Engineering Co | Carbonylation process and novel transition metal catalysts |
| DE2928314A1 (de) * | 1979-07-13 | 1981-02-12 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| FR2478078A2 (fr) * | 1980-03-12 | 1981-09-18 | Rhone Poulenc Ind | Procede d'hydroformylation des olefines |
| GB2085874B (en) * | 1980-09-04 | 1984-08-08 | Johnson Matthey Plc | Hydroformylation of olefins |
| DE3301591A1 (de) * | 1983-01-19 | 1984-07-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen hydroformylierung olefinisch ungesaettigter verbindungen |
| DE3341035A1 (de) * | 1983-11-12 | 1985-05-23 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3413427A1 (de) * | 1984-04-10 | 1985-10-17 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3420491A1 (de) * | 1984-06-01 | 1985-12-05 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| US4578523A (en) * | 1985-05-29 | 1986-03-25 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
-
1985
- 1985-12-24 DE DE19853546123 patent/DE3546123A1/de not_active Withdrawn
-
1986
- 1986-11-18 YU YU1967/86A patent/YU45381B/xx unknown
- 1986-12-11 KR KR1019860010601A patent/KR890003750B1/ko not_active Expired
- 1986-12-12 RO RO125839A patent/RO95854B/ro unknown
- 1986-12-13 EP EP86117394A patent/EP0226988B1/de not_active Expired - Lifetime
- 1986-12-13 ES ES198686117394T patent/ES2037006T3/es not_active Expired - Lifetime
- 1986-12-13 AT AT86117394T patent/ATE73122T1/de not_active IP Right Cessation
- 1986-12-13 DE DE8686117394T patent/DE3684113D1/de not_active Expired - Fee Related
- 1986-12-17 JP JP61299065A patent/JPS62153238A/ja active Granted
- 1986-12-17 IE IE328886A patent/IE59957B1/en not_active IP Right Cessation
- 1986-12-17 HU HU865260A patent/HUT42047A/hu unknown
- 1986-12-17 CS CS869413A patent/CS264286B2/cs unknown
- 1986-12-17 ZA ZA869473A patent/ZA869473B/xx unknown
- 1986-12-23 AU AU66896/86A patent/AU598502B2/en not_active Ceased
- 1986-12-23 BR BR8606417A patent/BR8606417A/pt not_active IP Right Cessation
- 1986-12-24 CA CA000526281A patent/CA1263407A/en not_active Expired
-
1988
- 1988-05-13 US US07/193,956 patent/US4808757A/en not_active Expired - Fee Related
-
1994
- 1994-10-24 HR HRP-1967/86A patent/HRP940741A2/hr not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| DE4207922A1 (de) * | 1992-03-13 | 1993-09-23 | Pharmatech Gmbh | Wasserloesliche einschlussverbindungen und verfahren zu deren herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0226988B1 (de) | 1992-03-04 |
| US4808757A (en) | 1989-02-28 |
| CS264286B2 (en) | 1989-06-13 |
| KR890003750B1 (ko) | 1989-10-04 |
| EP0226988A3 (en) | 1989-04-12 |
| CA1263407A (en) | 1989-11-28 |
| IE59957B1 (en) | 1994-05-04 |
| KR880007419A (ko) | 1988-08-27 |
| AU6689686A (en) | 1987-06-25 |
| YU196786A (en) | 1988-02-29 |
| HUT42047A (en) | 1987-06-29 |
| RO95854B (ro) | 1988-10-31 |
| RO95854A (ro) | 1988-10-30 |
| YU45381B (en) | 1992-05-28 |
| JPS62153238A (ja) | 1987-07-08 |
| JPH0517213B2 (enrdf_load_stackoverflow) | 1993-03-08 |
| EP0226988A2 (de) | 1987-07-01 |
| HRP940741A2 (en) | 1997-06-30 |
| BR8606417A (pt) | 1987-10-13 |
| ES2037006T3 (es) | 1993-06-16 |
| ZA869473B (en) | 1987-08-26 |
| ATE73122T1 (de) | 1992-03-15 |
| IE863288L (en) | 1987-06-24 |
| AU598502B2 (en) | 1990-06-28 |
| CS941386A2 (en) | 1988-09-16 |
| DE3684113D1 (de) | 1992-04-09 |
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| Publication | Publication Date | Title |
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